5-Hydroxyisoindoline-1,3-dione → 5-Hydroxy-2,3-dihydro-1H-isoindol-1-one

HRID 78313Notes

Reaction equation

HRID 78313 reaction equation
[OH:1][C:2]1[CH:12]=[C:6]2[C:7]([NH:9][C:10](=[O:11])[C:5]2=[CH:4][CH:3]=1)=O>CC(O)=O.[Zn]>[OH:1][C:2]1[CH:12]=[C:6]2[C:5](=[CH:4][CH:3]=1)[C:10](=[O:11])[NH:9][CH2:7]2

Participants

4

Reactant 1

HCID 105589505-Hydroxyisoindoline-1,3-dione

Product 1

HCID 225942075-Hydroxy-2,3-dihydro-1H-isoindol-1-oneYield 20.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-hydroxyphthalimide (19.8 g, 121 mmol) in AcOH (500 mL) was slowly added zinc dust (47.6 g, 729 mmol) in portions, then the mixture was heated at the reflux temp. for 40 min., filtered hot, and concentrated under reduced pressure. The reaction was repeated on the same scale and the combined oily residue was purified by column chromatography (1.1 Kg SiO2; gradient from 60% EtOAc/40% hexane to 25% MeOH/75% EtOAc) to give 5-hydroxyisoindolin-1-one (3.77 g): TLC (100% EtOAc) Rf 0.17; HPLC ES-MS m/z 150 ((M+H)+).

Workup

  1. temperaturethe mixture was heated at the reflux temp
  2. filtrationfiltered hot
  3. concentrationconcentrated under reduced pressure
  4. customthe combined oily residue was purified by column chromatography (1.1 Kg SiO2; gradient from 60% EtOAc/40% hexane to 25% MeOH/75% EtOAc)

Sources & evidence

ORD record
ord-d52158a8ae1a4db5a07b5d86205de0bf
Source dataset
uspto-grants-2014_09
Patent number
US08841330B2

Reaction notes

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